Guided  Gravel Tuscany  Bike Tour

Ride the famous ‘strade bianche’ white gravel roads of Tuscany, explore the medieval towns and enjoy world-famous Tuscan food and wine on this dream trip – join one of our planned departure

Pienza in the heart of val d’Orcia, Montalcino brunello wine, Siena the Gotham gothic city and Gaiole the Eroica town… what else?

The Strade Bianche of Tuscany is truly something special due to the region’s rolling vistas and fine wines make this a must-see destination if you love gravel cycling. Strade bianche  is Italian for “white roads,” and it comes from the color of the dry limestone gravel that lifts into a fine white dust that lingers along the race course.

These white, dusted roads are home to one of pro racing’s biggest dates, with steep climbs and full-blown attacks at every bend:  Strade Bianche professional race 

After the successful of our self guided Bike Tour in 2021 we decided to offer the guided version  selecting the more appropriate sections from  that race, from the Eroica itinerary that often coincide with Francigena path
The Permanent Route of L’Eroica is a unique experience that allows you to live the adventure of L’Eroica all year round,  anyway we offer the tour from March to November.
Traditional L’Eroica course  starts in the town of Gaiole on the first Sundays of October, anyway we love the Montalcino spring edition.

Hotels are all different experiences: old convent in Pienza, a wine producer relais in Montalcino, a villa in Siena and a castle in Gaiole

The pool at each hotels (except Siena) will be well appreciated after those epic day

This trip is designed for gravel bikes,
You can Bring your non-strong partner: great trekking e-bike are available and suitable for the itinerary 
Or non-riding partner along: we have guided daily activities available for non-riders. 

Carbon frame GRAVEL bike or  E-bike are perfect to face this tour
Choose between  Scott Gravel Addict  20  Or Scott  E-SUB Cross 10

Gravel Tuscany Bike tour’s Wow Moments

  • Shadow the hilly path of L’Eroica, Tuscany’s internationally recognized vintage bike race
  • 3 King’s wines: Vino Nobile di Montepulciano, Brunello di Montalcino, Chianti classico
  • Explore the undulating white gravel roads of Tuscany—the famed strade bianche—and immerse yourself in Italy’s most classic cycling local
  • Rest day in Siena with its countless monuments to take you back in time

If you are a gravel lover but no match with our dates we have the self guided version


Pienza & Bagno Vignoni

Meet at Chiusi-Chianciano train station at 12.00 (a stop on all major Florence-Rome lines).
Transfer to Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets
Check into your rooms at your hotel, which occupies a 15th-century convent in the center of town.
At 15.00 Meet your guides during a bike-fitting session and get to know the rest of the group. OPTIONAL (depends on time taken in the bike fitting) short ride to Bagno Vignoni:
a thermal spa town that dates back to Roman times, and Madonna di Vita Leta chapel
Distance 25 km /15 miles
12 km asphalt and 13 km gravel - Easy to Moderate
Welcome dinner at la Bandita townhouse


Montepulciano & Vino Nobile

Your tour starts with a circular ride from Pienza.
You pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as The Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany and enjoy the first espresso, overlooking the roads we just conquered. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces.
After a light lunch you deserve a wine tasting at our favorite cellar juts out of town – cantine Dei or Montemercurio.
Relaxing a while sipping a glass of Nobile wine… it’s time to continue: next stop is the village of Monticchiello, the quintessential Tuscan hill town.
distance 51 km /31,5 miles : 17 km asphalt and 34 km gravel - moderate difficulty
Dinner on your own

Pieve a Salti & Brunello Land

To get from Pienza to Montalcino we select the sections of Eroica called Lucignano d'asso and Pieve A Salti. You leave Pienza and after 6 km on paved road you will take the white road toward Cosona and reach the little hamlet of Lucignano - a caffè espresso at the little shop emporio - is a must. Once you reach the paved road you ride only one km and start the other Eroica gravel section Pieve a Salti - so beautiful landscape. 9 km up and down in the rural countryside! arrive in Buonconvento by lunch time. Now you have to face the climb to the famed wine town of Montalcino Tuscany’s most celebrated wine region. a total of 10 km: 5 on paved and 5 km on gravel all through vineyards and wineries.
In Montacino enjoy a light lunch and we will introduce to this legendary story, at every year Welcome Brunello with special tile.
We ask you the last effort to get to Pass Lume spento, the higher point of Montalcino, and enjoy the downhill to the wine relais Podere Brizio, where you will overnight.
Tonight dinner at Brizio pairing the dishes with rosso and Brunello they produce.
distance 48 km /25 miles: - km asphalt and - km gravel - moderate difficulty
Lodging at Podere Brizio in Montalcino

Castiglion del Bosco & Siena

L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the hardman mentality. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica
From Tavernelle reach Castiglion del bosco gravel section- Castiglion del bosco is the biggest brunello winery & farm belonging to Ferragamo, the famous Italian fashion designer - once in Bibbiano another section called la Piana and reach Murlo after 30 km- caffé & visit! shortly you will face another famous Eroica section to Radi, with some steep yet short up and down.
Light lunch is planned at Ville di Corsano
Now the last 12 km on secondary paved road to Siena
distance 58 km /35 miles: 32 km asphalt and 24 km gravel - moderate to challenge
Lodging at hotel Villa str in Siena
Dinner at Babazuf

Siena gothic city

extra day in Siena – rest or sightsee
Today is a rest day but for gravel addicted we will provide a map, gpd track for a glorious loo at Montagnola senese
The golden age of Siena was in the medieval period, it is quintessentially a Gothic city! You can dedicate the day to explore the town: The elaborate Duomo, the prized Palazzo Pubblico - seat of civil government but also houses the city's museum, the shell shape Piazza del campo and all the best-known paintings of the sienese School.
the most famous manifestation of sienese tradition and pride is the twice yearly Palio.
This exciting horserace is run in the piazza del Campo every July 2 and August 16, ostensibly as celebrations of the Virgin's visitation and Assumption respectively
Dinner on your own

Gaiole, the Eroica town

Today the destination is the town where the Eroica starts
After your gourmet breakfast, head out into magical Chianti. You will exit form Siena via a eroica gravel section Pieve a Bozzone, Vico dArbia making your way through wheat fields before we hit the vineyards of this celebrated wine region. Reach Pianella after 15 km. Form here you will take a long glourios section to Canonica A Cerreto, Vagliagli- all road through chianti classico vineyards - Counting castles and old hilltop hamlets! Get in Radda in Chianti for lunch time after 38 km ride - mostly gravel.
now you have only 8 km to Gaiole following the Eroica path via san donato in Perano and Vertine, 2 small enchanting borgo distance 46 km /28,5 miles
12 km asphalt and 34 km gravel - moderate to challenge
Lodging at the charming Hotel castello spaltenna
dinner on your own

Chianti hills - Castello di Brolio

Today is consecrated to explore all the villages and hamlet of Chianti Senese- start from your "castle di Spaltenna" in Gaiole and reach Castello di Brolio after 10 km - here the caffé at agribar in front of winery is a must: all cyclists, locals and visitors seems to meet there.
after you can ride into the gravel section of Eroica, is short and then you will ride on very secondary scenery roads until Castelnuovo Berardenga, it worth a visit and if you are there for lunch time offer many options.
Wine tasting Felsina
back to the saddle and encounter other small borgo: San Gusmé and villa a Sesta - back to Brolio: to return to Gaiole you have 2 options, one road downhill and flat so somewhat easy, or challenge uphill to Castagnoli, downhill to castello di Meleto.
distance 54 km /33,5 miles 44 km asphalt and 10 km gravel - moderate to challenge-
Farewell dinner at il Pievano

Arrivederci, a presto

Farewell breakfast at Spaltenna castle
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il Chiostro - Pienza
Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool.

Villa STR - Siena
Villa STR is a converted 19th-century villa that retains the charm and ambiance of its former origins as a private residence. The decoration in the recently renovated public areas bears the hallmarks of Italian classical design. It is just outside the ancient walls of the historic center of Siena, this hotel is a 10-minute walk from Piazza del Campo. In the summer you can appreciate the silence of the garden and the beauty of the flowers. Breakfast is served here in the summer months.
Castello di Spaltenna - Gaiole in Chianti
Castello di Spaltenna offers an exclusive atmosphere amidst a unique landscape. Located in the heart of the Chianti Classico wine region, the manor’s luxurious guestrooms offer any possible comfort along with wonderful views over the valley. Just on hill out of Giaole in Chianti - few meters - restaurant Pievano

gravel bike tour map

Price & Inclusions


Cost: Euro 2890  per person (price based on double accommodations)

single supplement euro 650
seven nights in excellent five, four & three-star superior hotels
seven  breakfasts,
2 wine tasting
4 dinners
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Keepsake Cicloposse water bottle
Sales taxes


Not Included
Bike Rental per entire tour
Gravel or E-bike euro 210


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